Alkyl-oxyacetyl-cyanamid and process of making same.



UNITED sra'rns PATENT OFFICE. j

ARNOLD H. C. HEITMANN AND ERIK C. CLEMMEN SEN, OF DETROIT,

' MICHIGAN, ASSIGNORS TO PARKE, DAVIS & COMPANY, OF DE- TROIT, MICHIGAN, A CORPORATION OF MICHIGAN.

ALKYL-OXYACETYL-CYAIJAMID AND PROCESS OF MAKING SAME.

Application filed November 25,1905. Serial No. 289.104.

To all whom it may concern:

Be it known that we, ARNOLD H. C. HEIT- JIANN, a citizen of the United States of America, and ERIK C. CLEMMENSEN, a subject of the King of Denmark, residing at Detroit, in the county of Wayne and Stateof Michigan, have invented certain new and useful Improvements in Alkyl-Oxyacetyl-Cyanamids and Processes of Forming Same, of which the following is a specification, reference being had therein to the accompanying drawings.

The invention relates to a new series of chemical bodies; and it consists, first, in the new substance, and, second, in the process of forming the same. The various compounds belongin to this new'series may be designated as al yl-oxyacetyl-cyanamids" and may be'formed by the condensation of an alkyloxyacetic acid and a cyan amid. This may be accomplished either directly -by the use of a suitable condensing agent or indirectly by treatment of substances which at somepoint in the reaction form the said'bodies which are subse' ucntly condensed. For commercial manu actu're We preferably emplo the latter method, as less costly materia s may be used. Forexample, in place of cyanamids we have discovered that other bodies, such as a thio-urea or a guanidin, may be mixed with an allxyl-oxyacetic'acid and treated with a condensing agent, resulting not in a con-' densation product of the said bodies, but an alkyl-oxyacetyl-cyanamid.

1 Preferred method of forming pr0duct.-A mixture, preferably in molecular proportion, is formed of an alkyl-oxyacetic acid (such as diethy-oxyacetic ester) and a urea-in which the oxygen has been replaced, (such as a thio.

urea,) together with a condensing agent, (such as an alkali alcoholate and preferably The said mixture is then preferably warmed for several hours, during which time the following reaction takes place:

The reaction product is carefully neutralized with an acid, preferably diluted acetic The alcohol is then distilled off and the Specification of Letters Patent;

' Patented March 13, 1906.

product crystallized out from the remaining aqueous solution. 7

x As a modification of the process above described a guanidin may be substituted for the thio-urea, (preferably a guanidin salt, such as guanidin-sulfo-cyanid,) the other substances remaining the saine and the reaction being as follows:

The reaction product is then carefully neu described.

preferably in molecular proportion, with a cyanam1d and a condensing agent, such as an alkali alcoholate, and upon warming the mlxture the following reaction takes place: (0 H,) COHUOOC H +NH CN+C H ONa= (C H COHCO.NNaCN+2C,l-I OH.

The reaction product is then separated, as

above described:

The bodies belonging to the new series are characterized bythe following properties: Theyv are crystalline, colorless, have a high melting-point, are soluble in Water and alcosoluble in other; organic solvents. Upon treating with a hydrolyzing agent, as dilute sulfuric ac-id, they are transposed into ureids of alkyl-oxyacetic acids by the following reactionr I 2(C,H5),COHCO.NHCN+8H,O=

Thus an important-use of the new product is in the manufacture of the said ureids.

The specific body (diethyl-oxyacetyl-cyantemperature of 235 centigrade.

'acetic acid is employed, this is meant also to include ,the ester.

What we claim as our invention is 1. A new body being a condensation prodnot of an alkyl-oxyace'tic acid and a cyanamid, which is characterized by being crystalline, colorless, having a high meltingtralized and separated in the manner above 'hol, but insoluble in ether, and only slightly amid) is further characterized by melting at a I W here in the claims the term alkyl-oxy-' point, being soluble in water and alcohol but I Where it is desired to employ the direct process, an alkyl-oxyacetic ester is mixed,

cm. ,ooHco.NHoN+cn,cooNa. Y

acid, is transposed into a nreid o1" nllq l-oxyinsoluble inethe-r and only slightly soluble in l other organic solvents; upon treating with :1- l hydrolyzing agent, such as dilute sulfuric! l acetic me. i

A new body which u condensation 1 product of (liethyl-oxyacctic acid and cyu-nl :unixtl, which is cluiructerizcd by being crys-j tnlliuc, colorless, soluhlc in water and alcol hol but insoluble in othc and only'slightly i soluble in other organic solvents and melting star teinpomturc of 235 centigrede; upon hydrolyzing, it is tmnsposcd into a ureid of diethyl-oxyncctic arid.

3. The process of forming nlkyl-oxyacctylanamids which consists in condensing an alhyhoxyocetic :LClLl and u cyanarnicl.

4 The process of forming :rllgyl-ox wcotyloyanuniids which consists in treating with it i condensing agent on alkyl-oxyucotic ncid and at urea, in which the oxygen has been suhstitntcdv l The process of forming diethyl-oXy-' :rcctyhcynnnmid which consists in treating with 21v condensing agent the ,(liethyl-oxy acetic ester and a cyanamicl.

6. The process of forming .nliethyl-oxy acetyl-cyunsmids which consists in. treating with it condensing agent dicthyl-oxyacetic ester and a ureu in which the been substituted.

' 7. The process of fox-mils: sll y3-oxyacctyl ureus whichv consists in forming a condensation product of an slkytoxyecotic acid and a cyonuniid and in hyclrolyzing said product to form. the nlkyhoxyacctyhuren.

8. The process of forming slkyl-oxyacetyt urcas which. consists in forming a condensew tion product of an alkyl-oxyacetic acid and u cyanamid by the treatment with a condensing agent of a mixture of the, said acid and a urea, in which the oxygen atom is replaced, and in then hydrolyzing the product to obtain the alkyl-oxyacetyl-urea.

In testimony whereof We afilxonrsignatures in presencc of two witnesses.

ARNOLD H C. HEITMANN. ERIK C. CLEE KMENSEN Witnesses:

Au REL] AS 3N1 LLE AN is, JAMES P. BARRY.

oxygen has u 

